Methanol → HCID 178452364, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(cis-4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarbonyl)piperazine-1-carboxylate (0.200 g, 0.377 mmol) was suspended in THF (3.77 mL), and the mixture was cooled to 0° C. under a nitrogen atmosphere. To this mixture was added a solution of 4-cyanobenzoyl isothiocyanate (0.078 g, 0.415 mmol) in 1.5 mL of THF. The reaction was stirred at RT for 30 minutes. PS-CDI (1.417 g, 1.884 mmol) was added (along with 6 mL of THF to account for swelling of the polymer-supported reagent) and the reaction was heated at 60° C. for 1 hour. The solids were filtered off (rinsing well with THF) and the filtrate was concentrated in vacuo. The residual material was purified via silica gel chromatography eluting with a gradient of 0% to 100% 90:10:1 DCM:MeOH:NH4OH, to provide tert-butyl 4-(cis-4-((E)-2-(4-cyanobenzoylimino)-6-(2-(piperidin-1-yl)ethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexane-carbonyl)piperazine-1-carboxylate as an orange solid (0.227 g, 88% yield). MS m/z=685.2 [M+H], calc 684.83 for C37H48N8O5.

Provenance & Evidence